Bisphenol derivative and its manufacturing method

Details Bisphenol derivative and its manufacturing method Bisphenol derivative and its manufacturing method

1994-08-22

2001-03-27

Trinh, Ba K. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S214000

Reexamination Certificate

active

06207841

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to a novel bisphenol derivative, in particular to a novel bisphenol derivative that can be used as an intermediate in the synthesis of useful substances and as an indicator of hydrogen ion concentration, and also to a method of manufacturing such a derivative.
BACKGROUND OF THE INVENTION
Conventionally known bisphenol derivatives may be represented by the following formula,
Methods of synthesizing these compounds are described in detail in Vijnana Parishad Anusandhan Patrica 3, 181-4 (1960), Experiencia 14, 257-68 (1958), J. Indian Chem. 40 (9), 785-8 (1963), Ann. Chim. 5, 1165-217 (1960), wherein a condensation reaction is performed between a cyclic acid anhydride and a phenol compound having a substituent group in the presence of an acid catalyst such as sulfuric acid.
This conventional method, however, suffered from the disadvantages that after synthesizing the phenol compound, a substituent group had to be introduced into the compound, the manufacturing process was long, and a good yield was not obtained.
The inventors, as a result of intensive studies carried out to resolve the above problems, found that the bisphenol derivative of this invention could be obtained in a short process and in high yield by reacting a Grignard reagent derived from a substituted phenol with cyclohexane-1,2-dicarboxylic acid anhydride.
SUMMARY OF THE INVENTION
It is therefore an object of this invention to provide a novel bisphenol derivative which can be used as an intermediate for synthesizing useful substances.
It is a further object of this invention to provide a method of manufacturing such a novel bisphenol derivative by a short process which gives a high yield.
The above objects are attained by a method of manufacturing the aforesaid bisphenol derivative characterized in that a Grignard reagent derived from the substituted phenol represented by the following formula,
is reacted with cyclohexane-1,2-dicarboxylic acid anhydride represented by the following formula,
In the above formula, R is a lower alkyl group, tetrahydropyranyl, methoxymethyl or trialkylsilyl, the benzene ring in the formula may be substituted by a lower alkyl group, and X is a halogen atom.
DETAILED DESCRIPTION OF THE INVENTION
The required Grignard reagent may easily be obtained by the method known in the art for synthesizing Grignard reagents, namely, by reacting the substituted phenol having the formula of
with metallic magnesium in ethyl alcohol or an ether-type solvent such as tetrahydrofuran.
In the above formula, R is a lower alkyl group, tetrahydropyranyl, methoxymethyl or trialkylsilyl, the benzene ring in the formula may be substituted by a lower alkyl group, and X is a halogen atom. As the lower alkyl group, one which has 1-6 carbon atoms is.
The reaction between the Grignard reagent and cyclohexane dicarboxylic acid anhydride may be performed at any temperature from −78° C. to the boiling point of the solvent, however, to obtain the bisphenol derivative in high yield, it is preferably performed at a lower temperature in this range.
The reaction solution obtained is neutralized by an aqueous solution of a common acid such as hydrochloric acid, and after separating the organic layer at a pH of 3 to 5, the product is purified by the usual methods of organic synthesis. This gives the following bisphenol derivative of the present invention.
The novel bisphenol derivative of this invention is useful as an additive for modifying polymers, and as an intermediate in the synthesis of physiologically active substances.
In addition, the compound obtained by eliminating the group protecting the phenolic hydroxyl group is also useful as an indicator for showing hydrogen ion concentration in aqueous solutions.
Moreover, if the phenolic hydroxyl group from which the protecting group has been eliminated is substituted by a functional group which can easily be dissociated and eliminated under acidic conditions, the compound exhibits excellent properties as a solution inhibitor for optical resists.
The method of manufacturing the novel bisphenol derivative of this invention makes it possible to obtain the target compound in high yield by means of a short process, and it therefore provides a bisphenol derivative with excellent cost performance. Further, the novel bisphenol derivative so obtained may in particular be used as an intermediate in the synthesis of useful substances, and as a hydrogen ion concentration indicator.


REFERENCES:
patent: 2-311473 (1990-12-01), None
Greene et al, “Protective Groups in Organic Synthesis,” 2ndedition, pp. 10-14, 413, John Wiley & Sons, Inc., 1991.

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